Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C-O Bond Cleavage.

J Org Chem

Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

Published: September 2024

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.4c01399DOI Listing

Publication Analysis

Top Keywords

reductive amidation
8
aryl fluorosulfates
8
c-o bond
8
nickel-catalyzed reductive
4
amidation aryl
4
fluorosulfates isocyanates
4
isocyanates synthesis
4
synthesis amides
4
amides c-o
4
bond cleavage
4

Similar Publications

In the wake of the pandemic, peptidyl protease inhibitors with Pro-based rigid Leu mimetics at the P position have emerged as potent drug candidates against the SARS-CoV-2 main protease. This success is intuitively attributed to the enhanced hydrophobic interactions and rigidity of Pro-based rigid Leu mimetics in the literature. However, the tertiary amide of proline P derivatives, which hinders the formation of a critical hydrogen bond with the enzyme active site, and the constrained PP conformation, which contradicts the protease preferred β-strand conformation, represent two overlooked disadvantages associated with these inhibitors over traditional inhibitors and, theoretically, should adversely affect their potency.

View Article and Find Full Text PDF

Objectives: This study aimed to determine whether incorporating nanostructured additives into bleaching agents enhances efficacy and reduces side effects while identifying gaps for further investigation.

Methods: A comprehensive search was conducted in electronic databases, including PubMed/Medline, Embase, Scopus, and ISI Web of Science. Two reviewers independently screened articles based on predefined criteria, resolving discrepancies through discussion or consultation with a third reviewer.

View Article and Find Full Text PDF

Discovery of 2-Pyrazolines That Inhibit the Phosphorylation of STAT3 as Nanomolar Cytotoxic Agents.

ACS Omega

January 2025

Laboratory of Chemical Biology, Department of Studies in Organic Chemistry, University of Mysore, Mysore, Karnataka 570006, India.

STAT3 has emerged as a validated target in cancer, being functionally associated with breast cancer (BC) development, growth, resistance to chemotherapy, metastasis, and evasion of immune surveillance. Previously, a series of compounds consisting of imidazo[1,2-]pyridine tethered 2-pyrazolines (referred to as ITPs) were developed that inhibit STAT3 phosphorylation in estrogen receptor-positive (ER+) BC cells. Herein, a new library of derivatives consisting of imidazo[1,2-]pyridine clubbed 2-pyrazolines (-) and its amide derivatives (-) have been synthesized.

View Article and Find Full Text PDF

The study evaluated the anti-hyperlipidemic effects of myrcenol and curzerene on a high fat diet induced hyperlipidemia rat model. Thirty male albino rats were fed on a high-fat diet for four months. The HFD-induced hyperperlipidemia rats were treated with rosuvastatin (10 mg/kg), curzerene (130 mg/kg) and myrcenol (100 mg/kg) for four weeks.

View Article and Find Full Text PDF

Quaternary ammonium compounds (QACs) have served as essential antimicrobial agents for nearly a century due to their rapid membrane-disrupting action. However, the emergence of bacterial resistance and environmental concerns have driven interest in alternative designs, such as "soft QACs", which are designed for enhanced biodegradability and reduced resistance potential. In this study, we explored the antibacterial properties and mechanisms of action of our newly synthesized soft QACs containing a labile amide bond within a quinuclidine scaffold.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!